Planta Med 2004; 70(3): 272-276
DOI: 10.1055/s-2004-818923
Letter
© Georg Thieme Verlag Stuttgart · New York

Antimicrobial Activity of 3-O-Acyl-(-)-epicatechin and 3-O-Acyl-(+)-catechin derivatives

Ki Duk Park1 , Yoon Sun Park1 , Sung Jin Cho1 , Won Suck Sun1 , Sung Han Kim2 , Do Hyun Jung2 , Jung Han Kim1
  • 1Department of Biotechnology, College of Engineering, Yonsein University, Seoul, Korea
  • 2Nutrex Technology, Seongnam-si, Kyounggi-do, Korea
Further Information

Publication History

Received: July 7, 2003

Accepted: November 9, 2003

Publication Date:
23 March 2004 (online)

Zoom Image

Abstract

As an exploratory investigation of antimicrobial promoting compounds, 3-O-acyl-(-)-epicatechins and 3-O-acyl-(+)-catechins possessing various aromatic groups and aliphatic chains of varying length from C4 to C16 for increasing lipophilicity were synthesized and tested for antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi. The (-)-epicatechin and (+)-catechin derivatives comprised of aromatic groups increased activity and derivatives with acyl chain groups of carbon atoms in the close vicinity of C8 to C10 showed strong antimicrobial activity (MIC = 2 - 8 μg/ml) against Gram-positive bacteria and weak activity against fungi. However, the activity decreased when the carbon chain length of the substituents was too short (C4 to C6) or too long (C16). These results suggest that the presence of lipophilic substituents with moderate sizes might be crucial for the optimal antimicrobial activity.